Propose two possible mechanisms for the following reaction. (Consider the possible sites of protonation in the molecule

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Propose two possible mechanisms for the following reaction. (Consider the possible sites of protonation in the molecule and the mechanistic consequences of each.) Devise an isotope-labeling experiment that might distinguish your two mechanisms. 

HCI, A -CH- CH- OH СООН

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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